Photocatalytic fluorosulfonylation of aliphatic carboxylic acid NHPI esters

Abstract

Sulfonyl fluorides have been increasingly favored by medicinal chemists and chemical biologists because of their unique reactivity and stability, but their synthetic methods still have certain limitations. Based on the SO₂ radical insertion/fluorination strategy, we have developed a novel method for photocatalytic induced synthesis of alkylsulfonyl fluorides (low to 1 mol% P.C. and up to 92% yield), which covers primary, secondary and tertiary aliphatic carboxylic acid NHPI esters, providing a facile method for the late-stage fluorosulfonylation of natural products and drugs. This method provides an efficient and reliable approach for the synthesis and application of alkylsulfonyl fluorides.